The production of isobutylene polymers from mixed C.sub.4 hydrocarbon feedstreams is generally known in the art. Typically, the reaction uses strong Lewis acids, i.e., titanium tetrachloride, aluminum trichloride, boron trifluoride. The resulting polyisobutylene has only one functional terminal double bond. It is often preferred to utilize AlCl.sub.3 as the polymerization catalyst in such processes and the prior art discloses a number of co-catalyst or catalyst promoters, including hydrogen chloride, for use under various conditions in isobutylene polymerization.
Representative disclosures include U.S. Pat. No. 2,957,930, which shows the use of 10 to 20% AlCl.sub.3 catalyst in the production of polyisobutylene from a C.sub.1 -C.sub.5 petroleum gas feedstock with 0.08 to 0.12 percent HCl, relative to AlCl.sub.3, used as a catalyst promoter. This reference notes that correspondingly small quantities of water vapor or chloroform, which can react with AlCl.sub.3 to release HCl, may also be used. British Pat. No. 1,195,760 (1970) discloses the production of olefin polymers by polymerization in the presence of the catalyst comprising a liquid complex of AlCl.sub.3, HCl and an alkyl benzene. Polymerization products include materials other than polyisobutylene and products with a narrow molecular weight distribution are disclosed in this reference.
U.S. Pat. Nos. 3,200,169 and 3,200,170 deal with reaction mixture separation methods after polymerization of propylene or butylene feeds utilizing an ammonia treatment process. HCl is disclosed in the references as a suitable catalyst promoter added to the reaction zone which contains an AlCl.sub.3 catalyst.
U.S. Pat. No. 3,997,129 discloses polybutenes from a C.sub.1 -C.sub.5 liquified refinery stream wherein the catalyst is solid particles of AlCl.sub.3 promoted with HCl qas or its equivalent. This process employs a static mixer for mixing catalysts and feed prior to conductinq polymerization.
U.S. Pat. No. 3,985,822 relates to the production of poly-n-butenes by use of AlCl.sub.3 promoted with HCl but the objective is to reduce the isobutylene content of the polymer product.
U.S. Pat. No. 3,119,884 discloses a series of vertical column reactors useful for polymerizing isobutylene and further discloses a catalyst system comprising AlCl.sub.3 and HCl or a substance which generates HCl. The catalyst system is described as an acid promoted AlCl.sub.3 catalyst. In such a system, a reaction between HCl and AlCl.sub.3 occurs to form H.sup.+ AlCl.sub.4 --which is the species that initiates polymerization. According to this process, one method of introducing catalysts and reactants is to have the three materials, i.e. AlCl.sub.3 HCl and liquid feed, enter the reactor through the same duct.
It is known also to prepare epoxidized olefins polymers by the reaction of a polymer derived from an olefin containing 2 to 12 carbon atoms and a peracid. U.S. Pat. No. 3,382,255 discloses the epoxidation of polybutene in heptane to which is added a 40% peracetic acid solution. The temperature is held between 25.degree.-30.degree. C. by external cooling. Suitable and typical peracids useful in the epoxidation include performic, peracetic, perbenzoic, perphthalic and others. Performic and peracetic acids are preferred.
A polymer of isobutylene prepared in presence of a typical catalyst such as aluminum chloride is normally monofunctional, having a double bond at one end of the polymer chain. The olefin structure is predominantly the trisubstituted type (R--CR.dbd.CHR), approximately 70%, and tetrasubstituted type (R--CR.dbd.CR.sub.2), approximately 20%. Small amounts of vinylidene (R--CH.sub.2 --CR.dbd.CH.sub.2) and terminal vinyl (R--CH.dbd.CH.sub.2) are present, approximately 10%. The major component of polybutenes prepared in the presence of aluminum chloride can be represented as (CH.sub.3).sub.3 --C--[CH.sub.2 --C(CH.sub.3).sub.2 --]n--CR.dbd.CHCH.sub.3. Some internal double bonds exist but these are not easily characterized. The olefin structure results in a compound which on epoxidation is relatively unreactive to many reagents because of steric hindrance.
Surprisingly, it has been found that epoxidized polybutenes comprising a trisubstituted epoxide structure, approximately 70%, and a tetrasubstituted epoxide structure, approximately 20%, and a 1,1-disubstituted or monosubstituted epoxide structure of approximately a content of about 10% can be reacted with a hydroxyl to form a hydroxyether in the presence of a catalyst selected from the group consisting of strongly acidic resin catalysts such as Amberlyst 15 (TM) useful for non-aqueous heterogeneous catalysis; catalysts with non-nucleophilic anions such as fluoboric acid and perchloric acid, which are not consumed through reaction with epoxide groups; and Lewis acids, for example, ZnCl.sub.2, SnCl.sub.2, SnCl.sub.4, TiCl.sub.3, TiCl.sub.4, AlCl.sub.3, SbCl.sub.5, BF.sub.3.sup..multidot. (C.sub.2 H.sub.5).sub.2 O, and FeCl.sub.3.
It is therefore an object of this invention to provide a process for preparing a hydroxyether terminated polybutene wherein the polybutene portion has a molecular weight of from about 200 to about 20,000.
It is another object of this invention to provide a hydroxyether terminated polybutene wherein the polybutene portion has a molecular weight of from 200 to 20,000 which can be used as a component of polyesters, polyurethanes, and other compounds useful for coatings, sealants, adhesives, and other applications.